Phosphorus oxychloride → 2-Chloro-6-(2-chlorophenyl)-5-(4-chlorophenyl)nicotinonitrile

HRID 916980Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 916980
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:13][C:12](=O)[C:11]([C:15]#[N:16])=[CH:10][C:9]=1[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1.O=P(Cl)(Cl)[Cl:26]>>[Cl:26][C:12]1[N:13]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[C:9]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[CH:10][C:11]=1[C:15]#[N:16]

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 219849076-(2-Chlorophenyl)-5-(4-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

Produkt 1

HCID 102371012-Chloro-6-(2-chlorophenyl)-5-(4-chlorophenyl)nicotinonitrile

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To the product of Step C of Example 129 (1.50 g, 4.40 mmol) was added POCl3 (5 mL, 53.6 mmol). The mixture was heated to 100° C. for 17 hours before concentrating in vacuo. The residue was dissolved in ethyl acetate and washed with NaHCO3 (saturated, aq.), water, dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (silica gel) eluting with 10% ethyl acetate/hexane affording product. MS (electrospray) m/e 360.9 MH+ (Rt=4.1 min LC/MS).

Aufarbeitung

  1. concentrationbefore concentrating in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with NaHCO3 (saturated, aq.), water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (silica gel)
  7. washeluting with 10% ethyl acetate/hexane affording product

Quellen und Nachweise

ORD-Eintrag
ord-ec141460397d48199b8704f716a29923
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07271266B2

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